It's New Year's Eve in Times Square. The ball has just lowered and lit up the sky with "Happy New Year," but our hero has helped changed it to read "Holly I'm Here" for a lovelorn street musician who hopes his message will reach his intended. Despite his good intentions, our hero, who claims he is Cupid, the Roman god of love, not unsurprisingly is placed in a mental institution. There he is placed under the care of Dr. Claire McCrae, an author of a book on love and relationships. After three months, claiming his real name is Trevor Pierce, he is released but placed directly under Dr. McCrae's care and responsibility. She requires him to attend her singles group therapy sessions on a regular basis so that she can monitor his progress. Trevor, who strongly believes in passion and chemistry, finds himself at direct odds with Claire's rather cold and clinical attitude towards love and relationships. Trevor meanwhile works towards attaining his first match.
Trevor sets up Claire's friend Riley with a social activist... who unfortunately turns out to be married. The cynical private investigator who exposed the activist's married state seems an unlikely successor, except to Trevor. Trevor also hooks up his boss/roommate Felix with a woman who turns out to be the mother of Lita's new boyfriend.
When Marshall, product of a sperm donation, hacks into the donor bank to find out about his dad, he learns about and then meets up with Clint, a boxing instructor, who he begins to take lessons from (without telling him who he is). He decides to set up his mom with Clint, in the hopes that they will hit it off together. Unfortunately, just about everything Clint is and stands for -- his political beliefs, his profession, etc., is at direct odds with her pacifist, leftist ideals. In the meanwhile, Claire has an unpleasant and unexpected house guest in her rather ditzy mother.
Trevor is talking on the phone with Claire as she goes home. Claire walks into her apartment to find it has been ransacked, and hangs up immediately. Trevor rushes over and finds that everything is ok, nothing is even missing, but Claire is still very nervous about her safety. In the meantime, Trevor talks with the locksmith, who happens to be an ex-con who has fallen in love with his attractive young parole officer... Never fear, Trevor is on the job: "One key to her heart, coming up!"
Joe, an Iraq war vet, has a problem. He has PTSD, and has been referred to Claire for examination. He wakes up at night after nightmares, and has written a large bundle of letters to a girlfriend he had in high school, which he's never sent. He picks the right time to throw them away, however, in the presence of Trevor, who reads them and arranges for the two to meet again, and things go smashingly. Cue the monkey wrench, though... Trevor's job is never simple.
Trevor attempts to unite a radio shock jock with one of his listeners, and Claire becomes involved with a statistics specialist from a dating bank.
In a riff on George Bernard Shaw's Pygmalion (the original play upon which the musical My Fair Lady was based), Trevor sets out to retrain a "lower class" massage therapist to make her more acceptable for the family of her "upper class" ex-boyfriend by connecting her with a dialogue coach to disguise her history. Also, Claire thinks she's onto a clue to Trevor's actual past, but is it a faux lead?